EP 2017260 A1 20090121 - Aldimines and compounds containing aldimine
Title (en)
Aldimines and compounds containing aldimine
Title (de)
Aldimine und Aldimin enthaltende Zusammensetzungen
Title (fr)
Aldimine et aldimine contenant des compositions
Publication
Application
Priority
EP 07112503 A 20070716
Abstract (en)
New aldimine compounds are claimed. Aldimine compounds of formula ((HX) m-A-(N=CH-C(R 1>)(R 2>)-CH(R 3>)-N(R 4>)(R 5>)) n) (I), are new. Either A : an amine residue after removing n primary aliphatic amino group and m HX group; or A together with R 7> : (n+2)-valent 3-20C-hydrocarbon, which optionally contains at least a heteroatom, preferably in the form of an ether oxygen or tertiary amine nitrogen; either n : 1-4, preferably 1 or 2; and m : 0-1; or m+n : 2-5; either R 1>, R 2> : univalent 1-12C-hydrocarbon; or R 1>R 2> : a bivalent 4-12C-hydrocarbon, whose one part is optionally substituted by 5-8C, preferably 6C carbocyclic ring; R 3> : H or 1-12C-alkyl, -arylalkyl or alkoxycarbonyl; R 4>, R 5> : univalent 1-20C-aliphatic, -cycloaliphatic or -arylaliphatic atoms, which is free of OH and optionally contains heteroatom in the form of ether-oxygen or tertiary amine nitrogen; R 4>R 5> : a bivalent 3-20C-aliphatic atoms, whose one part is optionally substituted by heterocyclic ring 5-8, preferably 6, ring atoms, where the ring is free of OH and contains optionally further heteroatom in the form of ether oxygen or tertiary amine nitrogen, adjacent to the nitrogen atom; X : O, S, NR 6>or NR 7>; R 6> : univalent 1-20C-hydrocarbon, which optionally contains at least a carboxylic acid ester-, nitrile-, nitro-, phosphonic acid ester-, sulfone or sulfonic acid ester group, or (-B 1>-(N=CH-C(R 1>)(R 2>)-CH(R 3>)-N(R 4>)(R 5>)) p) (II); p : 0-10000; and B 1> : (p+1)-valent hydrocarbon, which contains optionally an ether-oxygen, tertiary amine nitrogen, OH, secondary amino or mercapto. Independent claims are included for: (1) another aldimine compound of formula ((HX 2>) m-A-(N=CH-C(R 1>)(R 2>)-CH(R 3>)-N +>(R 10>)(R 4>)(R 5>)) n) (IX), obtained by protonating or alkylating (I); (2) the preparation of (I); (3) the preparation of an aldehyde compound of formula (O=CH-C(R 1>)(R 2>)-CH(R 3>)-N(R 4>)(R 5>)) (IV) obtained from an aldehyde formula (O=CH-CH(R 1>)(R 2>)) (V) or (O=CH-CH-R 3>) (VI), a secondary aliphatic amine of formula (NH-R 4>-R 5>) (VII), preferably dimethylamine, diethylamine, diisopropylamine, dibutylamine, diisobutylamine, N-methylcyclohexylamine, N-methyl-benzylamine, N-isopropyl-benzylamine, N-tert.butyl-benzylamine, dibenzylamine, pyrrolidine, piperidine, morpholine or 2,6-dimethylmorpholine; (4) an aldimino group containing compound (VIII) obtained by reacting (I) (in which m is 1) with at least a compound (IX) containing a reactive group, which can undergo addition reaction with the HX group in (I); and (5) a hardenable composition comprising (I) or (VIII) and at least a polyisocyanate. R 10> : H or 1-20C-alkyl, cycloalkyl or arylalkyl; X 2> : O, S, NR 11>or NR 7>; and R 11> : univalent 1-20C-hydrocarbon, which optionally contains at least a carboxylic acid ester, nitro, nitrile, phosphonic acid ester, sulfone or sulfonic acid ester, or (-B 1>-(N=CH-C(R 1>)(R 2>)-CH(R 3>)-N +>(R 10>)(R 4>)(R 5>)) p) (IXa).
Abstract (de)
Gegenstand der vorliegenden Erfindung sind in einem ersten Aspekt Aldimine der Formel (I). Diese Aldimine eignen sich insbesondere als latente Härter in härtbaren Zusammensetzungen, insbesondere in ein- oder zweikomponentigen Isocyanatgruppen aufweisenden Zusammensetzungen. Sie lassen sich aufgrund der vorhandenen reaktiven Gruppe zu Aldimingruppen-haltigen Verbindungen der Formel (X) und (XII) umsetzen, welche ein weiterer Aspekt der vorliegenden Erfindung darstellt. Die Aldimine, bzw. die Aldimingruppen-haltigen Verbindungen, lassen sich vor allem in Kleb- und Dichtstoffe, aber auch in Beschichtungen verwenden und lassen sich leicht aus gut erhältlichen Grundstoffen herstellen und weisen eine gute thermische Stabilität auf. Ihre tertiäre Aminogruppe weist eine überraschend niedrige Basizität auf und kann unter Umständen in chemischen Reaktionssystemen eine katalytische Wirkung entfalten.
IPC 8 full level
C07C 251/08 (2006.01); C07D 213/53 (2006.01); C07D 295/125 (2006.01); C08G 18/28 (2006.01); C09J 175/02 (2006.01)
CPC (source: BR EP US)
C07C 251/08 (2013.01 - BR EP US); C07D 295/108 (2013.01 - BR EP US); C07D 295/13 (2013.01 - BR EP US); C08G 18/12 (2013.01 - BR EP US); C08G 18/3256 (2013.01 - BR EP US); C08G 18/4812 (2013.01 - BR EP US); C08G 18/6696 (2013.01 - BR EP US); C08G 18/808 (2013.01 - BR EP US); C09D 175/04 (2013.01 - BR EP US); C09J 175/04 (2013.01 - BR EP US); C08G 2190/00 (2013.01 - BR EP US)
Citation (search report)
- [X] DE 4212795 A1 19931021 - AGFA GEVAERT AG [DE]
- [A] EP 1384709 A1 20040128 - SIKA TECHNOLOGY AG [CH]
- [A] EP 1772447 A1 20070411 - SIKA TECHNOLOGY AG [CH]
- [X] ERIC C. BROWN ET AL: "Modular syntheses of multidentate ligands with variable N-donors: applications to tri- and tetracopper(I) complexes", DALTON TRANS., 8 June 2007 (2007-06-08), pages 3035 - 3042, XP002464027
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC MT NL PL PT RO SE SI SK TR
Designated extension state (EPC)
AL BA HR MK RS
DOCDB simple family (publication)
EP 2017260 A1 20090121; BR PI0814427 A2 20150106; BR PI0814427 B1 20200924; CN 101687775 A 20100331; CN 101687775 B 20150506; EP 2178828 A1 20100428; EP 2178828 B1 20190626; ES 2744533 T3 20200225; JP 2010533677 A 20101028; JP 2014221770 A 20141127; JP 5563451 B2 20140730; JP 6141799 B2 20170607; RU 2010105241 A 20110827; RU 2489421 C2 20130810; US 2010101455 A1 20100429; US 2012220736 A1 20120830; US 8252859 B2 20120828; US 8519038 B2 20130827; WO 2009010522 A1 20090122
DOCDB simple family (application)
EP 07112503 A 20070716; BR PI0814427 A 20080716; CN 200880023766 A 20080716; EP 08786166 A 20080716; EP 2008059267 W 20080716; ES 08786166 T 20080716; JP 2010516495 A 20080716; JP 2014121813 A 20140612; RU 2010105241 A 20080716; US 201213462347 A 20120502; US 45195508 A 20080716